Tris(hydroxymethyl)aminomethane → HCID 54689850, compound

Participants

Reaction Steps

[4-(5-Cyano-4-hydroxy-6-oxo-3a,6,7,7a-tetrahydro-thieno[2,3-b]pyridin-3-yl)-benzylideneaminooxy]-acetic acid (0.035 g, 0.1 mmol) and C-pyridin-2-yl-methylamine (0.013 g, 0.12 mmol) were added to a suspension of resin bound 1,3-dicyclohexyl carbodiimide (0.166 g, 1.2 mmol/g, 0.2 mmol) and 1-hydroxybenzotriazole hydrate (0.013 g, 0.1 mmol) in 1:1 dichloromethane/N,N-dimethylacetamide (4 mL) at room temperature. After complete reaction, resin bound trisamine (4.7 mmol/g, 0.053 g, 0.25 mmol) was added to the reaction mixture, shaken at room temperature for 1 hour, filtered, concentrated and purified by RP-HPLC to afford the title compound. MS (ESI) m/e 457.8 (M−H)+; 1H NMR (500 MHz, DMSO-d6): δ ppm 12.15 (br s, 1H), 8.52–8.56 (m, 2H), 8.42 (s, 1H), 7.88 (dt, J=10.5, 1H), 7.61 (d, J=10, 2H), 7.51 (d, J=10, 2H), 7.38–7.43 (m 2H), 7.01 (s, 1H), 4.65 (s, 2H), 4.50 (d, J=5, 1H).

Provenance & Evidence